The separation process in cylinder and unswept compression ramp induced shock wave turbulent boundary layer interactions was examined using a conditional-analysis of wall pressure fluctuation measurements. The tests were performed in a Mach 5 blow down tunnel under adiabatic wall temperature conditions. The conditional analysis showed that the instantaneous separation position is at or close to the instantaneous separation shock foot in these interactions. The separation line as indicated by traditional surface tracer methods is at, or close to, the downstream boundary of a region of intermittent separation. The dynamics of the separation bubble in the unswept compression ramp flow field were also examined and initial results suggest that the motion of the separation point and reattachment point locations are correlated. The preliminary results indicate the reattachment point is at its downstream locations when the separation shock is at its upstream locations. Keywords: Flow separation bubble; Turbulent flow; Shock waves; Turbulent boundarylayer; Unsteady flow; Reattached flow; Flowfield interactions.